A table with four pointed feet.
Not the one I meant but a right answer so keep it. A bench with four pointed feet.
A right answer, keep it. Add the table with a single large support.
Add the table with one center leg.
Correct. Now add the box floating above a crown.
No, not that one. This one is a square that sits above a mountain range.
A square, not a diamond.
Correct. Now add the pyramid with the diamond balanced at the very top.
No, the other shape with a diamond at the top.
Correct. Now, lastly, add the head and shoulders of an animal leaning in from the right.

Outcome: successful
Speaker comments: we got there in the end, but the bot was all over the place, multiple bizarre guesses and non-sensical responses to my prompts